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Record Information
Version1.0
Creation Date2014-09-17 20:02:27 UTC
Update Date2016-11-09 01:09:14 UTC
Accession NumberCHEM003906
Identification
Common NameTris(2-chloroethyl)phosphate
ClassSmall Molecule
DescriptionTris(2-chloroethyl) phosphate (TCEP) is a chemical compound used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates. It was included in January 2011 in the European Chemicals Agency (ECHA) list of Substances of Very High Concern (SVHC) due to its being toxic for reproduction. Substances in the list of SVHCs are those for which ECHA is considering imposing a requirement for authorization for some or all uses.
Contaminant Sources
  • ECHA Toxic for reproduction
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Plasticizer
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Phosphoric acid, tris(2-chloroethyl)esterChEBI
Tri(2-chloroethyl) phosphateChEBI
Tris(2-chloroethyl) orthophosphateChEBI
Tris(beta-chloroethyl) phosphateChEBI
Tris(chloroethyl)phosphateChEBI
Phosphate, tris(2-chloroethyl)esterGenerator
Tri(2-chloroethyl) phosphoric acidGenerator
Tris(2-chloroethyl) orthophosphoric acidGenerator
Tris(b-chloroethyl) phosphateGenerator
Tris(b-chloroethyl) phosphoric acidGenerator
Tris(beta-chloroethyl) phosphoric acidGenerator
Tris(β-chloroethyl) phosphateGenerator
Tris(β-chloroethyl) phosphoric acidGenerator
Tris(chloroethyl)phosphoric acidGenerator
Tris(2-chloroethyl)phosphoric acidGenerator
Fyrol cefMeSH
Genomoll PMeSH
Tri(chloroethyl)phosphateMeSH
Tris(2-chlorethyl)orthophosphateMeSH
Chemical FormulaC6H12Cl3O4P
Average Molecular Mass285.490 g/mol
Monoisotopic Mass283.954 g/mol
CAS Registry Number115-96-8
IUPAC Nametris(2-chloroethyl) phosphate
Traditional Nametris(2-chloroethyl)phosphate
SMILESClCCOP(=O)(OCCCl)OCCCl
InChI IdentifierInChI=1S/C6H12Cl3O4P/c7-1-4-11-14(10,12-5-2-8)13-6-3-9/h1-6H2
InChI KeyHQUQLFOMPYWACS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentTrialkyl phosphates
Alternative Parents
Substituents
  • Trialkyl phosphate
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoskeleton
  • Membrane
  • Microsome
  • Mitochondrial Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Mismatch repairNot Availablemap03430
Cell cycleNot Availablemap04110
Base excision repairNot Availablemap03410
AnticonvulsantsNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.57 g/LALOGPS
logP1.36ALOGPS
logP2.11ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity56.13 m³·mol⁻¹ChemAxon
Polarizability23.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03l0-6090000000-2ff653400988c9855017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l0-8290000000-817dc166ce8aa6781835View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-052e00872865bfaf0dfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-9c8aaade1730674178f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-0590000000-3f032bbcfc9677fd9a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3910000000-0d7df033a49f8fb9a53eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-06r2-9580000000-6cc979ed4f6998e16219View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesTris(2-chloroethyl) phosphate is used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTris(2-chloroethyl)_phosphate
Chemspider IDNot Available
ChEBI ID35037
PubChem Compound ID8295
Kegg Compound IDC14445
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19462192